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The Five Ways to Bring Your Boss a Problem

You can tell where someone is in their career by how they bring you a problem, not how hard it is. The five levels from something is broken to I already fixed it, and the jump that actually gets you promoted.

The Five Ways to Bring Your Boss a Problem

I manage a team now, which mostly means people bring me problems all day. After a few years of it, I have noticed I can place almost anyone on the seniority ladder from a single thing. Not how hard their problem is. How they hand it to me.

Same bug, five very different sentences

Give five people the identical broken thing and you get five completely different messages.

  1. “Something is broken.” That is the whole report. True, and almost useless. At this level you are basically a very expensive smoke detector.
  2. “Something is broken, and I think it is the payments service.” Now there is a direction. You actually looked. Good.
  3. “Payments is down, I think it is the retry config, and we could either bump the timeout or add a circuit breaker.” Now you are handing me options. I can make a real decision with this.
  4. “Payments is down, it is the retry config, and of the two fixes I would go with the circuit breaker, because bumping the timeout just moves the problem to next week.” This is the one. You did the thinking and you took a position. You are not asking me to solve it, you are asking me to sanity check you.
  5. “Payments was down, it was the retry config, I shipped the circuit breaker, here is the PR. Just keeping you in the loop.” You did not bring me a problem at all. You brought me a heads up.

The jump nobody wants to make

Most people get stuck between 2 and 3. They will investigate forever but stop right before proposing anything, because proposing a fix means being wrong out loud. That fear is the entire ceiling. The people at 3 and 4 are wrong all the time. They just decided they would rather be wrong with a plan than safe with a shrug.

The gap from 4 to 5 is a different animal. That one is not about skill, it is about trust. New folks should live at 4, because shipping a production fix with no heads up when nobody knows you yet is how you lose the room fast. As trust builds, you earn your way up to 5.

What I actually say

When someone brings me a level 1 or a level 2, I try not to solve it. I ask the slightly annoying question instead: what have you tried, and what would you do if I were on vacation? Nine times out of ten the answer is already a level 3 or 4. They had the plan the whole time, they just did not trust it enough to say it out loud. Half of leveling up is realizing your hunch was a real proposal all along.

The best part is this has nothing to do with your title. I have watched interns operate at level 4 and staff engineers park at level 1. It is the same muscle as the part of the job AI cannot grade, deciding which problem matters and being willing to take a position on it before you knock on someone’s door.

Pick your level. Then bring me that one.

Thanks for reading!

I write about frontend craft, React, TypeScript, and the web. Found this useful? Let me know.

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